Bis-phenylol silanes



Patented Sept. 23, 1952 'BIs-PHENYLo sILANEs john L'. Speier, Jr.,,Pittsburgh, Pa., assignor to Dow Corning Corporation, Midland, Mich" a corporation of Michigan No Drawing. Application September 18, 1950,?Se- I rial No. 185,513. In Great'Britain November The presentinvention relates to the production or dimethylbis phenyloDsiljanes.

Phenoxysilanes such as tetraphenylsilicate have been described in the literature. The compounds produced in accordance with the method of the present inventionjare distinguished from the phenoxysilanes in that the hydroxyl substituent on the benzene ring is not boridedlto the silicon. Both the hydroxyl andthe silicon jsubstituents are on the ring; In accordance with the method of the present invention, a dimethylbis-halophenoxysilane is reacted by contactingit with molten alkali metal in the presence of trimethylchlorosilane. The reaction product is then hydrolyzed, whereby there is obtained a dimethylbis(phenylol)silane. The dimethylbishalophenoxysilane may be substituted with a methyl radical in the ring if desired. This raw material may be prepared by adding two equivalents of ohlorophenol or chlorocresol to one equivalent of dimethyldichlorosilane. Upon heating, hydrogen chloride is expelled, with the formation of the desired product. Alternatively, dimethyldiethoxysilane may be employed instead of the dimethyldichlorosilane. In this case ethyl alcohol is expelled upon heating. If desired, the product may be purified by distillation, though this is unnecessary for the present process. Thus, these materials are of the following general formula:

n enmsi[o 1 1-2 The product actually obtained is probably as follows:

7! c-nmsiog Si(CH3)g L 12 ii Claims. (Cl. 260-4482) In order to contact the halophenoxy'silane-with the molten'alkali metal in the presence 'of-trimethylchlorosilane, various operative procedures may be followed. Thus, the moltenalkali metal may be in suspension in the trimethylchlorosilane and the halophenoxysilane added to the suspen sion. Alternatively, the trimethylchlorosilane and the halophenoxysllane may be mixed and the mixture added to the molten alkali metal;- either alone or in suspension in an inert hydrocarbon solvent such as octane or'toluenep' Molten sodiumand potassium or 'alloysthereoi are preierredin accordance herewith; due to the low melting points thereof. Lithium is not a preferred species, since its melting point is substanv tially higher.

The resulting dimethylbis-phenylolsilane so obtained is insoluble in cold water, soluble in cold alcohol, and soluble in boiling water. When the bis-phenols are reacted with aqueous formaldehyde, cleavage of the phenolic group from the silicon occurs. However, the products do react with hexa-methylenetetramine to form the expected phenolformaldehyde condensation resins containing silicon. Resins so prepared are thermosetting in character and after filling with a suitable filler, such as asbestos, may be molded under heat and pressure in accordance with conventional methods employed for the molding of phenol-formaldehyde resins.

p The compounds hereof, furthermore, are active bactericides. Thus, the compounds hereof, in a concentration of 0.025 per cent by weight, are more effective in controlling the growth of Staphylococcus aureus than phenol at a concentration of 0.125 per cent.

Example 1 A mixture was prepared of one molecular equivalent of parabromophenol and one equivalent of diethoxydimethylsilane. The mixture was heated to distill the ethanol produced and the excess diethoxydimethylsilane. There was thereby obtained dimethylbis-parabromophenoxysilane which had a boiling point of 219 C. at 1 mm. A mixture was prepared of 122 grams of this compound and grams of chlorotrimethylsilane. The mixture was added to 30 grams of molten sodium suspended in 200 cc. of boiling toluene containing 10 grams of chlorotrimethylsilane. The mixture was refluxed for one-half hour, following which it was cooled and filtered. The toluene was removed by distillation. grams of a viscous material was obtained (theory equal 117 grams). This product was then distilled to 390 C. at 20 mm. to remove low boiling Examplez- The procedure of Example 1 was repeated with the Substitution of p-chlorophenol fonrtha bromophenol of Example 1. tTheesame 'product. was obtained.

Example 3 The procedure of Example 1 was repeated, employing; 3t-methyl.-4.-.chlorophenol.in place. of..the psbromophenoh 1. The following :proriuctwas ob This compound "has a': meltingrrpoint :of 1-208 to: 2109; (L

- That: whichis claimedfisz.

1. Thezmethod: .ofsrproducing, qdimethyibis (phenylol);si1anes .whicln; comprises.":- reacting a dim'ethylbisvhaiophenoxysilane: ofi-theafornmla:

4 in which R represents an alkyl radical, X represents a halogen atom, and n is an integer from to 1 inclusive, with trimethylchlorosilane by contacting ..the..two with. an .alkali metal, and hydrolyzingfthe reaction product.

2. The method in accord with claim 1 wherein .Rwepresents a methyl radical.

' 3. The method in accord with claim 1 wherein .1; xiissselected from the group consisting of chlorine and bromine atoms.

1 QllTlr'e; methodmf" producing dimethylbis- I..(-pheriylol)isilanes;which comprises reacting a dimethylbis-halophenoxysilane of the formula X z in which R represents an alkyl radical, X representszahalogem atom,..and n is aninteger from 0 to 1 inclusive, .with;trimethylchlorosilane by contactingtheatwo.in..liquid.phase with a molten alkali metal, .andshydrolyzing .the. reaction. prod- I 5;.-Thel.method.-.in. accordance. with claim 4 wherein Rerepresentsa methyl radical.

6?...The .methodflin. accordance. with...claim 4 wherein..X .is selected. from.v the. group consisting of chlorine and bromine atomsi JOHN. LKSPEIER, J R.

i Ne reirences. cited. 

1. THE METHOD OF PRODUCING DIMETHYLBIS(PHENYLOL) SILANES WHICH COMPRISES REACTING A DIMETHYLBIS-HALOPHENOXYSILANE OF THE FORMULA 